Patent GB-895001-A (GB)
Title: Improvements in or relating to photographic reproduction
IPC: C08F2/48
Filed: 1959-08-14
Abstract: A coating composition for electrophotographic plates comprises a natural or synthetic resin and a photo-conductive arylene-oxazole, arylene-thiazole or arylene-imidazole substituted in the 2-position by an aromatic or heterocyclic group.  A sensitizing dyestuff or chlorophyll may also be present. Specified solvents are methanol, methylene chloride, glycol monomethyl ether, acetone, methyl ethyl ketone, benzene and toluene.  The support may be metal (e.g. aluminium), glass or a resin, and may be coated by, e.g. spraying or roller coating.ALSO:Photo-conductive resinous compositions comprise one or more arylene-oxazoles, arylenethiazoles or arylene-imidazoles substituted in the 2-position by an aromatic or heterocyclic group, together with a resin, and optionally a dyestuff, as in Specification 853,880.  Many suitable azoles are listed.ALSO:Condensed azoles of the formulae <FORM:0895001/IV (b)/1> where R is an aromatic or heterocyclic radical, R1 is the residue of an aromatic ring, and R2 is H, alkyl, aryl or aralkyl, are made by condensing RCHO with the appropriate o-substituted arylamines and simultaneously or successively dehydrogenating the products.  The nucleus R and/or R1 can be substituted by alkyl, halogen, hydroxy, alkoxy, methylenedioxy, nitro, amino, dialkylamino or acetylamino. Sulphonamide groups can be introduced into the products by successive treatment with chlorsulphonic acid and ammonia or an amine. Benzthiazoles can be made from RCHO and o-amino-thiophenols or o-aminothiosulphuric acids, the products being dehydrogenated by boiling in alcohol or acetic acid.  To obtain benzoxazoles, the Schiffs bases from RCHO and o-aminophenols are dehydrogenated with lead tetra-acetate. Benzimidazoles are prepared from RCHO and o-phenylenediamines (optionally substituted by R2) in the presence of nitrobenzene or m-dinitro-benzene.  Compounds prepared by these methods are: benzthiazoles: 2 - phenyl, 2 - (p - methoxy - phenyl), 2 - (p - aminophenyl), 2 - p - dimethyl - aminophenyl), 2 - phenyl - 6 - methyl, 2 - (p - methoxyphenyl) - 6 - methyl, 2 - (p - amino - phenyl) - 6 - methyl, 2 - (p-acetylaminophenyl) - 6 - methyl, 2 - (p - dimethylaminophenyl) - 6 - methyl and its x-sulphonyl chloride, x-sulphonamide, x-ethylsulphonamide and x-sulphomoramide, x-methylsulphonamide, x-ethylsulphon-and x - sulphomorpholide, 2 - (p - diethylaminophenyl - 6 - methyl and its x - sulphonyl chloride, x - dimethylsulphon amide and x - diethylsulphonamide, 2 - (31 - methoxy - 41 - hydroxy - phenyl) - 6 - methyl, 2 - (31 - hydroxy - 41 - methoxyphenyl) - 6 - methyl, 2 - (21- methoxy - 61- hydroxyphenyl) - 6 - methyl, 2 - (31 : 41 - dihydroxyphenyl) - 6 - methyl, 2 - phenyl - 6 - methoxy, 2 - (p - methoxyphenyl) - 6 - methoxy, 2 - (p - dimethylamino - phenyl) - 6 - methoxy, 2 - (p - diethylamino - phenyl) - 6 - methoxy, 2 - phenyl - 6 - dimethyl - amino, 2 - (p - methoxyphenyl) - 6 - dimethyl - amino, 2 - (o -, m -, or p - nitrophenyl) - 6 - dimethylamino, 2 - (p - dimethylaminophenyl) - 6 - dimethylamino, 2 - (p - diethylaminophenyl) - 6 - dimethylamino and 2 - (31 : 41 - methylene - dioxyphenyl) - 6 - dimethylamino; benzoxazoles: 2 - phenyl, 2 - (p - methoxyphenyl), 2 - (p - dimethylaminophenyl), 2 - (p - diethylamino - phenyl), 2 - (p - methoxyphenyl), 2 - (p - di - methylaminophenyl) - 6 - methyl, 2 - (p - di - ethylaminophenyl) - 6 - methyl, 2 - (p - methoxy - phenyl) - 5 - chloro, 2 - (p - dimethylamino - phenyl) - 5 - chloro and 2 - (p - diethylamino - phenyl) - 5 - chloro; benzimidazoles: 2 - (p - aminophenyl), 2 - (31 - methoxy - 41 - hydroxy - phenyl), 2 - (p - diethylaminophenyl), 1 - methyl - 2 - (31 : 41 - methylenedioxyphenyl), 1 - methyl - 2 - (p - dimethylaminophenyl), 1 - methyl - 2 - (p - diethylamino - phenyl), 1 - methyl - 2 - (41 - hydroxy - 11 - naphthyl), 1 - methyl - 2 - (p - dimethylaminophenyl) - 6 - methyl, 1 - methyl - 2 - (31 : 41 - methylene - dioxyphenyl) - 5 - methyl, 1 - methyl - 2 - (p - dimethylaminophenyl) - 5 - methyl, 1 - methyl - 2-(p-diethylaminophenyl)-5-methyl, 1-methyl-2-(p-methoxyphenyl)-5-nitro, 1-methyl-2-(p-dimethylaminophenyl)-5-nitro, 1-methyl-2-(p-diethylaminophenyl)-5-nitro, p 1-ethyl-2-(o-hydroxyphenyl), 1-phenyl-2-(p-dimethylaminophenyl, 1-phenyl-2-(p-diethylaminophenyl), 1-(p-dimethylaminophenyl)-2-(o-hydroxyphenyl)-6-chloro, 1 : 2 - bis - (p - dimethylaminophenyl) - 6 - chloro, 1 - benzyl - 2 - (p - hydroxyphenyl), 1 : 5 - dimethyl - 2 - (21 - pyrryl) and 1 : 5 - dimethyl - 2 - a  - naphthyl; naphtho - 21, 31 : 4, - imidazoles: 2 - (p - dimethylaminophenyl) and 2 - (a  - pyridyl); naphtho - 11, 21 : 4 : 5- imid - azoles: 1 - methyl - 2 - (o - hydroxyphenyl) and 1 - ethyl - 2 - (p - dimethylaminophenyl) - 71-methoxy.  2 - (41 - phenylureido - phenyl) - 6 - methyl - benzthiazole and 2 - (31 - phenylureido - 41 - dimethylamino-phenyl)-6-methyl-benzthiazole are prepared from phenyl isocyanate and the corresponding amines.  2 - (31 - amino - 41 - dimethylamino - phenyl) - 6-methyl-benzthiazole is made by nitrating 2-(41 - dimethylaminophenyl) - 6 - methyl - benz - thiazole and catalytically hydrogenating the product.  Phenanthro - 91, 101 : 4, 5 - oxazoles are made by heating phenanthraquinone with RCHO and formamide.  There are thus obtained the 2-phenyl, 2-(p-chlorophenyl), 2-(p-methoxyphenyl), 2-(p-diethylaminophenyl) and 2-(21-furyl) compounds.